There's no telling why a great but straightforward book might become a lousy movie—or why a film version of a "difficult" novel might be a classic.

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"I hold no brief for Hollywood," Raymond Chandler wrote in a 1945 piece for The Atlantic, after he had been in the city of angels for a little over two years. Already, he said, he was bored with it all. And that, in his mind, was unforgiveable. He continued:

An industry with such vast resources and such magic techniques should not become dull so soon. An art which is capable of making all but the very best plays look trivial and contrived, all but the very best novels verbose and imitative, should not so quickly become wearisome to those who attempt to practice it with something else in mind than the cash drawer. The making of a picture ought surely to be a rather fascinating adventure. It is not; it is an endless contention of tawdry egos, some of them powerful, almost all of them vociferous, and almost none of them capable of anything much more creative than credit-stealing and self-promotion.

Chandler had good reason to be disenchanted with the film industry. In the span of two years, his novels had been the inspiration for no fewer than three films—with decidedly uneven results. There was The Falcon Takes Over, an adaptation of Farewell, My Lovely that exiled Chandler's timeless detective, Philip Marlowe, and replaced him with the duo of the Falcon and his sidekick, Goldy Locke. Timeto Kill did the same with Chandler's The High Window, except this time around, Marlowe was transformed into Michael Shayne, for the seventh and last installation of the Michael Shayne series. The best of the lot: Murder, My Sweet, also based on Farewell, My Lovely (apparently, that particular title had just too good a plot to pass up). But though the film at last brought Marlowe to the screen, name and cigarettes intact, it too left much to be desired. New York Times critic Bosley Crowther may have called it "fairly close to the source," but fans of Chandler's writing would be hard-pressed to find the essence of the meticulously ethical detective they love in the depiction of Marlowe as "a private detective who would take a dollar from anyone, with no questions asked" and is "just a shade above his clients, who might be politely called questionable characters." Little wonder Chandler was less than thrilled with Hollywood's book-to-screen prowess.

Little wonder, perhaps. But consider: Chandler's works seem ready-made for the big screen. The plots. The characters. The dialogue. It's like Shakespeare or Jane Austen—or Sherlock Holmes or James Bond—in its ease of access. All you need to do, it seems, is lift from one medium to the other, and you're near guaranteed a hit. Why, then, hadn't it worked out quite so nicely?

Now, take the counter-case: David Mitchell's Cloud Atlas, to be released in just a few weeks. Where Chandler seemed initially destined for cinematic glory, Mitchell has said himself that he had always considered his book to be unfilmable. Parallel, interrupted, unfinished plots. A narrative that goes back and forth in time, from a futuristic, sci-fi landscape to a 19th-century sailing vessel. From the South Pacific, to the United States, to England, Korea, and back again. It's a headache to follow, let alone to contemplate filming in any way that makes any sort of sense. And yet, if initial accounts are accurate, this one could be bound for Matrix-like box office glory—and whatever the film's eventual success, Mitchell himself couldn't be more pleased. He has called the Wachowskis' approach "ingenious" and said that, whenever he tries to recall what his vanity-publisher character looked like in his head as he was writing, "all I see now is Jim Broadbent's face smiling back, devilishly." And is he okay with that? It, "as it happens, is fine by me."

One novel that seems made for Hollywood gold; one that seems altogether imponderable. The one, with an author who dismisses the whole film business as trivial and contrived; the other, with an author who applauds the ingenuity and depth of the directors' vision—and quips that "This could be one of those movies that are better than the book!" Where's the rhyme and where's the reason?

The failure of Chandler to translate to the screen isn't all that remarkable: Far more seemingly perfect books fail to make the transition than succeed. More intriguing is the converse, those novels that seem far from Hollywood in form and substance and yet somehow manage to make it through despite the odds.

Cloud Atlas is but one of a long list of titles deemed unfilmable, by author and movie moguls alike, until it was, well, filmed. There's the perennial contender, James Joyce's Ulysses, which has now come to the screen not once but twice, first with the 1967 Ulysses—deemed "as faithful and fine a screen translation of James Joyce's Ulysses as anyone with taste, imagination and a practical knowledge of this medium could ask"—and more recently, with the 2003 Bloom, an Irish adaptation that won its Molly Bloom, Angeline Ball, a best actress award at the Irish Film and Television Awards. There is the seemingly uncapturable Naked Lunch, not only filmed by David Cronenberg in 1991 but then hailed as "a remarkable meeting of the minds" and an "ingenious approach to [Burroughs's] material," and the unwieldy Catch-22, which Mike Nichols tackled fresh off of his Graduate success—and Vincent Canby termed "quite simply, the best American film I've seen this year." There is The Sound and the Fury, Faulkner's multi-viewed telling that came off in 1959, with Yul Brynner taking on Jason Compson. (To say the movie was based on the book as such, however, would be to stretch the point a bit. Chandler would have nodded his head in commiseration at the liberties taken with plot and characters both—and this time around, critics agreed. Crowther cited the original line of the title, "a tale told by an idiot, full of sound and fury, signifying nothing" as the most accurate description of the film itself.) And, if we're to believe the rumors, there will soon be a take on As I Lay Dying as well, in the hands of James Franco. (Though Franco film rumors do tend to get ahead of themselves, at least as far as unfilmable novels are concerned. His adaptation of Cormac McCarthy's Blood Meridianfell through before it came to much.)

Of course, the track record has been uneven. David Lynch's 1982 Dune may not have been entirely successful, but at least Lynch got the thing made. You can't say the same for Alejandro Jodorowsky, who aborted his own attempt, which would have included Orson Welles, Salvador Dalí, Mick Jagger, Gloria Swanson, and Alain Delon (now that, I would have seen), or for Ridley Scott, who was set to direct the film before Lynch came into the picture. And that film version of Vonnegut's Cat's Cradle you may have heard about? Though Leonard DiCaprio's production company, Appian Way, optioned the book, it has since gone through several writers and directors—including, at one point, Darren Aronofsky—but has yet to see the light of day. James Franco isn't the first to try his hand at Blood Meridian. Others who have picked up and then dropped off the project include Ridley Scott and Todd Field. And that's not to mention the biggest never-made of all: John Kennedy Toole's A Confederacy of Dunces. Over the years, the versions that have started and died include Harold Ramis's take, which would have starred John Belushi; adaptations that were set to star John Candy and Chris Farley; a version to be directed by John Waters; one to be written by Stephen Fry; an early 2000s Steven Soderbergh attempt, to have been directed by David Gordon Green, with Will Ferrell playing the part of Ignatius J. Reilly; and, most recently, a James Bobin version with Zach Galifianakis in the lead.

And what is it exactly that would prevent a Confederacy of Dunces: The Movie? It would seem to be far closer to a Chandler than a Mitchell, a film with linear plot, vivid characters, and expressive dialogue. Something that just cries out for a satirical take that so many of its stars-to-be seem all too perfect to give. It shouldn't be anywhere near unfilmable—a far cry from a Mallone Dies or a Pale Fire or a 100 Years of Solitude or any of the titles that have been deemed so unwieldy that they've never even been attempted—and yet, even with the best actors and directors, the most deep-pocketed producers and ardent supporters, it has failed to get that green light.

There will be great books. There will be great films. Sometimes the two will intersect. And always, there will be unfilmable novels that shock us by just how filmable it ended up being after all.

Sometimes, we know exactly why a book doesn't come to the screen. Try as they might, not a Marlon Brando or a Samuel Goldwyn, a Billy Wilder or a Jack Nicholson or an Elia Kazan, a Leonardo DiCaprio or a John Cusack or a Tobey Maquire or a Jerry Lewis could get The Catcher in the Rye into film-worthy shape. Salinger—and now, his estate—would simply never allow it. As he once explained, Catcher is, "a very novelistic novel. There are readymade 'scenes'—only a fool would deny that—but for me, the weight of the book is in the narrator's voice, the non-stop peculiarities of it, his personal, extremely discriminating attitude to his reader-listener, his asides about gasoline rainbows in street puddles, his philosophy or way of looking at cowhide suitcases and empty toothpaste cartons—in a word, his thoughts." And while Salinger may have found the process of seeing the book transformed onto the screen exciting in theory, practically, it was "if not odious, at least odious enough to keep me from selling the rights." Sometimes, we know exactly why a book does survive the transition. In the case of Cloud Atlas, we know just what the Wachowskis went through to get Mitchell on board—and precisely why he thinks his book is safe in their hands. But can we ever know in advance what will work and what won't?

Probably not.

There is no formula, nothing that you can point to as steering you toward a tremendous success, a colossal failure, or—as most often happens—some forgettable mediocrity in between. There will be great books. There will be great films. Sometimes, if we are lucky, the two will intersect. Sometimes they won't. And always, there will be that one unfilmable novel that will shock us all by just how filmable it ended up being after all, so that once we see it, we can't help but ask, whatever made us think it couldn't be done in the first place?

Even Chandler, the eternal Hollywood pessimist, acknowledged, "That these magics do somehow, here and there, by another and even rarer magic, survive and reach the screen more or less intact is the infrequent miracle which keeps Hollywood's handful of fine writers from cutting their throats."

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